Organosilane compounds

ABSTRACT

Novel compounds of the formula ##STR1## or siloxane oligomers thereof, wherein R 1  is an alkyl group containing 1 to 4 carbon atoms, 
     
         (CH.sub.3).sub.3 Si or Z(OC.sub.x H.sub.2x).sub.m 
    
     where x is 2 to 4, m is 1 to 20, Z is hydrogen, an alkyl group containing 1 to 18 carbons or an acyl group containing 1 to 4 carbon atoms; a is 0 to 2; R 2  is an alkyl group containing 1 to 18 carbon atoms; R 3  is an alkyl group containing 1 to 18 carbon atoms; R 4  is an alkyl, aryl or arylalkyl group containing 1 to 12 carbon atoms, a carboxy-substituted alkyl group containing 1 to 4 carbon atoms, 
     
         (C.sub.x H.sub.2x O).sub.m Z 
    
     where x, m, and Z are as defined above, or oxygen provided only one R 4  is oxygen; R 5  is an alkyl, aryl or arylalkyl group containing 1 to 22 carbon atoms; X is halide; and Y is nitrogen, phosphorus or sulfur. The novel compounds are useful for inclusion in a detergent composition for imparting soil release benefits to metallic and vitreous surfaces contacted therewith.

BACKGROUND OF THE INVENTION

This invention relates to novel organosilane compounds.

Various quaternized substituted organosilane compounds are known. Forexample, British Pat. No. 686,068 discloses compounds having the generalformula

    [(R.sub.3 SiCH.sub.2).sub.a NR.sup.1.sub.b H.sub.4-a-b ]Y

where R is an alkyl, monocyclic aryl hydrocarbon or alkoxy radical, R¹is an alkyl, alicyclic hydrocarbon or monocyclic aryl hydrocarbonradical or hydroxy alkyl radical, a is 1 to 2, b is 0 to 3 with a+bbeing not greater than 4 and Y is an acid anion. British Pat. No.1,164,581 discloses compounds of the general formula

    [(RO).sub.a Si(CH.sub.3).sub.3-a CH.sub.2 N(CH.sub.3).sub.3 ].sup.+Br.sup.-

wherein R is an alkyl radical containing 1 to 6 carbon atoms or a phenylradical and a is 1 or 2. U.S. Pat. No. 3,730,701 discloses compounds ofthe formula

    (CH.sub.3 O).sub.3 Si(CH.sub.2).sub.3 N.sup.+(CH.sub.3).sub.2 R R.sup.1

where R is an alkyl radical having 11 to 22 carbon atoms and R¹ ishalide. These compounds are said to be useful as intermediates in theformation of organosilicon resins, catalysts and emulsifying agents (B.P. 686,068), as modifiers for organopolysiloxane resins and oils (B. P.1,164,581) and for the control of algae (U.S. Pat. No. 3,730,701).

U.S. Pat. No. 3,560,442 discloses cross-linking agents of formula

    (RO).sub.3 SiCH(R')N(R")R'"

where R is an alkyl radical having 1 to 4 carbon atoms, R' is hydrogen,an alkyl radical having 1 to 6 carbon atoms or a phenyl radical, R" ishydrogen or a methyl radical and R'" is hydrogen, alkyl, cycloalkyl,aminoalkyl, (methylamino)-alkyl or (dimethylamino)-alkyl radical with 1to 6 carbon atoms or a radical of formula

    (RO).sub.3 SiCH(R')-- or (RO).sub.3 SiCH(R')N(R")CH.sub.2 CH.sub.2 --.

british Pat. No. 882,067 discloses compounds of formula ##STR2## whereinR is a substituted or unsubstituted alkyl group, R' and R" are hydrogen,or organic radicals, preferably alkyl, aminoalkyl, cyanoalkyl,hydroxyalkyl, carbo-alkoxyalkyl, carboxyalkyl or aryl radicals, or themonovalent grouping ##STR3## where X is an alkoxy radical or the oxygenatom of a siloxylidyne radical .tbd. Si -- O --, or R' and R" togetherwith the nitrogen atom may form a heterocylcic ring, Y is a hydroxy,alkoxy, alkyl or aryl radical, Z is an alkoxy, alkyl, or aryl radical, cis 1 or 2, b is 0 to 2, and c+b is not more than 3.

It has now been found that the novel compounds as hereindescribed areuseful as an additive to a detergent composition. Commonly assignedcopending patent applications "Organosilane-Containing DetergentComposition" and "Organosilane-Containing Anionic Detergent Composition", both by Heckert and Watt, Ser. No. 570,534, filed Apr. 22, 1975 andSer. No. 570,533, filed Apr. 22, 1975, respectively disclose detergentcompositions containing a class of organosilanes. When metallic orvitreous surfaces are washed with a detergent composition containing theorganosilane, a thin polymeric coating of the organosilane is depositedupon the washed or rinsed surfaces. The polymerized coating imparts asoil release benefit to the surface, thereby making the surface easierto clean in subsequent washings.

It is an object of this invention to produce novel organosilanecompounds.

It is another object of this invention to produce organosilane compoundshaving utility in a detergent composition.

These and other objects will become apparent from the description tofollow.

As used herein all percentages and ratios are by weight unless otherwiseindicated.

SUMMARY OF THE INVENTION

An organosilane having the formula ##STR4## or siloxane oligomersthereof, wherein R₁ is an alkyl group containing 1 to 4 carbon atoms,

    (CH.sub.3).sub.3 Si or Z(OC.sub.x H.sub.2x).sub.m

where x is 2 to 4, m is 1 to 20, Z is hydrogen, an alkyl groupcontaining 1 to 18 carbons or an acyl group containing 1 to 4 carbonatoms; a is 0 to 2; R₂ is an alkyl group containing 1 to 18 carbonatoms; R₃ is an alkyl group containing 1 to 18 carbon atoms; R₄ is analkyl, aryl or arylalkyl group containing 1 to 12 carbon atoms, acarboxy-substituted alkyl group containing 1 to 4 carbon atoms,

    (C.sub.x H.sub.2x O).sub.m Z

where x, m, and Z are as defined above, or oxygen provided only one R₄is oxygen; R₅ is an alkyl, aryl or arylalkyl group containing 1 to 22carbon atoms; X is halide; and Y is nitrogen, phosphorus or sulfur.

DETAILED DESCRIPTION OF THE INVENTION

This invention relates to organosilane compounds having the formula##STR5## or siloxane oligomers thereof wherein R₁, x, m, Z, R₂, a, R₃,b, R₄, R₅, Y and X are as defined immediately above.

Preferably X is chloride or bromide, a is 0 or 1, R₃ is a methyl group,R₄ is an alkyl group containing 1 to 4 carbon atoms and R₅ is an alkyl,aryl or arylalkyl group containing 6 to 12 carbon atoms.

It should be understood that the R₄ in the above formula and theformulae to follow may be the same or different. It should further beunderstood that when Y is sulfur, there will be only one R₄ substituent.Also, when one R₄ is oxygen or, under basic conditions, the anion of acarboxylic acid substituted alkyl, the counter ion X⁻ is not extant. The1 to 4 carbon atoms in the carboxy-substituted alkyl group is inclusiveof the carboxyl group.

The preparation of the above compounds is described in the succeedingparagraphs.

The compounds when a is 0 and R₁ is an alkyl group and R₄ is an alkyl,aryl or arylalkyl group are prepared by the following route:

    __________________________________________________________________________     X.sub.3 SiH                                                                             +  CH.sub.2  R.sub.3                                                                        ##STR6##                                                                         X.sub.3 SiCH.sub.2 R.sub.3                        (trihalosilane)                                                                            (olefin)      (trihaloalkylsilane)                                X.sub.3 SiCH.sub.2 R.sub.3                                                              +  X.sub.2                                                                                  ##STR7##                                                                         ##STR8##                                                       (halogen)     (alpha-haloalkyltrihalosilane)                      ##STR9##  +  3 R.sub.1 OH                                                                             ##STR10##                                                                        ##STR11##                                                      (alcohol)     (alpha-haloalkyltrialkoxysilane)                    ##STR12##                                                                               +  (R.sub.4).sub.1 or 2 YR.sub.5                                                            ##STR13##                                                                        ##STR14##                                                      (tertiary amine,                                                                            [alpha-(trialkylammonio)alkyl-                                  tertiary phosphine,                                                                         trialkoxysilane halide,                                         or dialkylsulfide)                                                                          alpha-(trialkylphosphonio)-                                                   alkyltrialkoxysilane halide, or                                               alpha-(dialkylsulfonio)alkyl-                                                 trialkoxysilane halide]                            __________________________________________________________________________

The trihalosilane is reacted with an olefin at 100° C. for 4 to 10 hoursunder a pressure of 50 to 300 psi. in the presence of a chloroplatinicacid or platinum catalyst to produce the trihaloalkylsilane. Thisreaction is reported by F. P. Mackay, O. W. Steward and P. G. Campbellin "Journal of the American Chemical Society, 79, 2764 (1957) and J. L.Speier, J. A. Webster and S. W. Barnes in Journal of the AmericanChemical Society, 79, 974 (1957).

The trihaloalkylsilane is then halogenated in a known manner by treatingit with halogen in the presence of light (such as that provided byordinary tungsten or fluorescent lamps). Preferably, halogenation iscarried out to only partial completion and a distillation is performedto recycle unreacted alkylsilane.

The resultant alpha-haloalkyltrihalosilane is reacted with a loweralcohol to produce the alpha-haloalkyltrialkoxysilane. At least threeequivalents of alcohol per equivalent of haloalkyltrihalosilane areadded slowly to the silane. The alpha-haloalkyltrihalosilane may bedissolved in an inert solvent, preferably hexane or pentane. (See W.Noll, "Chemistry and Technology of Silanes", Academic Press, New York,1968, page 81 for the alcoholysis of halosilanes.)

One equivalent of the alpha-haloalkyltrialkoxysilane is reacted with oneequivalent of the tertiary amine, tertiary phosphine, or dialkylsulfideto produce the organosilane. An inert solvent, preferably of highdielectric constant, may be used. The reaction is carried out attemperatures of from 40° C. to 100° C. and a time of 2 to 10 hours forthe reaction of the bromopropyltrialkoxysilane and 120° C. to 140° C.for 2 to 20 hours for the reaction of the chloropropyltrialkoxysilane.

When a is 1 or 2, the preparation of the compounds is essentially thesame except for the use of an alkyl substituted silane as the startingreactant.

The organosilanes when at lease one R₄ is a carboxysubstituted alkylgroup are prepared in the same manner except for the last reaction step.Here, a tertiary amine, tertiary phosphine or dialkylsulfide having acarboxy-containing alkyl group(s) is reacted with thealpha-haloalkyltrialkoxysilane at 50° C. to 200° C. for 2 hours to 20hours. Such carboxysubstituted tertiary amines, tertiary phosphines, anddialkylsulfides are produced by reacting

    R.sub.4 YHR.sub.5 or HYR.sub.5 (where Y is sulfur)

with

    X(CH.sub.2).sub.1-3 COOH

in the presence of base at elevated temperatures, e.g. 50° C. to 150° C.

When at least one R₄ is

    (C.sub.x H.sub.2x O).sub.m Z

with x, m and Z as defined above, the compounds are produced in themanner given above except for the last reaction step. Thus,alpha-haloalkyltrialkoxysilane is reacted with a tertiary amine,tertiary phosphine, or dialkylsulfide where at least one substituent is

    (C.sub.x H.sub.2x O).sub.m Z

the reaction takes place at a temperature of 50° C. to 200° C. and atime of from 2 to 10 hours.

Organosilanes where one R₄ is oxygen are prepared by following thereactions outlined above up to the last reaction step. At this point, adialkyl amine, dialkyl phosphine or alkylthiol is reacted with thehalosilane at 50° C. to 200° C. for from 4 to 10 hours and then withbase to produce an intermediate tertiary amine, phosphine, or dialkylsulfide. These intermediates are then reacted with H₂ O₂ at 20° C. to100° C. or preferably O₃ in an inert solvent at -80° C. to 20° C. toyield the organosilane.

The compounds that follow are illustrative of these compounds

(C₂ H₅ O)₃ SiCH(C₈ H₁₇)N⁺(CH₃)₂ C₁₂ H₂₅ Cl⁻

(CH₃ O)₃ SiCH(C₁₈ H₃₇)N⁺(C₂ H₄ COOH)₂ CH₃

(c₃ h₇ o)₂ ch₃ siCH(C₁₂ H₂₅)N⁺(C₂ H₄ OH) (CH₃)₂ Cl⁻

(C₄ H₉ O)₃ SiCH(C₃ H₇)N⁺[(C₂ H₄ O)₁₀ H]₂ C₆ H₁₃ Br⁻

(CH₃ O)₃ SiCH(C₁₀ H₂₁)N⁺[₂ H₄ O)₂ C₄ H₉ ](CH₃)C₆ H₅ Br⁻

(CH₃ O)₃ SiCH(CH₃)N⁺[(C₂ H₄ O)₃ COC₂ H₅ ](C₂ H₅)₂ Br⁻

(C₂ H₅ O)₂ CH₃ SiCH(C₈ H₁₇)N⁺(O)⁻(CH₃)₂

(ch₃ o)₃ siCH(C₈ H₁₇)P⁺(CH₃)₃ Cl⁻

(CH₃ O)₂ CH₃ SiCH(CH₃)P⁺(C₃ H₆ COOH)₂ C₁₄ H₂₈ C₆ H₅ Cl⁻

(C₂ H₃ O)₃ SiCH(C₁₀ H₂₁)P⁺(C₂ H₄ OH)C₄ H₉ Cl⁻

(CH₃ O)₃ SiCH(C₃ H₇)P⁺(O)⁻(CH₃)C₁₂ H₂₅

(ch₃ o)₃ siCH(C₈ H₁₇)P⁺[(C₂ H₄ O)₆ H]₂ CH₃ Cl⁻

(C.sub. 2 H₅ O)₃ SiCH(C₆ H₁₃)P⁺[(C₃ H₆ O)₂ C₁₈ H₃₇ ](CH₃)₂ Cl⁻

(CH₃ O)₃ SiCH(CH₃)S⁺(CH₃)C₁₆ H₃₃ Br⁻

(C₂ H₅ O)₂ CH₃ SiCH(C₁₂ H₂₅)S⁺(C₃ H₆ COOH)CH₃ Cl⁻

(CH₃ O)₂ C₁₆ H₃₃ SiCH(C₂ H₅)S⁺(C₂ H₄ OH)C₂ H₅ Cl⁻

(CH₃ O)₃ SiCH(C₁₀ H₂₁)S⁺(O)^(-C) ₅ H₁₁

(c₂ h₅ o)₃ siCH(C₄ H₉)S⁺[(C₃ H₆ O)₁₀ H]C₆ H₅ Cl⁻

C₂ h₅ o)₃ siCH(CH₃)S⁺[(C₂ H₄ O)₂₀ C₂ H₅ ]CH₃ Br⁻

when R₁ is

    Z(OC.sub.x H.sub.2x).sub.m

the organosilane is formed in the same manner as the above compoundswhen R₁ is an alkyl group with the exception that

    Z(OC.sub.x H.sub.2x).sub.m OH

is used in place of

    R.sub.1 OH

during the alcoholysis of the halosilane. This reaction takes place at25° C. to 200° C. at 4 hours to 20 hours.

A mixture of R₁ OH and

    Z(OC.sub.x H.sub.2x)OH

can be used in the alcoholysis step to prepare an organosilane havingdifferent substituents on the silicon atom.

The following compounds illustrate the organosilane when at least one R₁is

    Z(OC.sub.x H.sub.2).sub.m.

[CH₃ (OC₂ H₄)₃ O]₃ SiCH(CH₃)N⁺(CH₃)₂ C₁₈ H₃₇ Cl⁻

[C₂ H₅ (OC₂ H₄)O]₂ CH₃ SiCH(C₂ H₅)N⁺(C₂ H₄ OH)₂ C₁₄ H₂₉ Cl⁻

[H(OC₄ H₈)₈ O]₃ SiCH(C₄ H₉)N⁺(C₂ H₄ COOH) (C₄ H₉)CH₂ C₆ H₅ Cl⁻

[CH₃ CO(OC₂ H₄)₂ O]₃ SiCH(C₂ H₅)N⁺(O)⁻(CH₃)C₁₀ H₂₁

[h(oc₃ h₆)₆ o]₃ siCH(C₁₂ H₂₅)N⁺[(C₂ H₄ O)₁₀ H]₂ CH₃ Br⁻

]C₁₂ H₂₅ (OC₂ H₄)O]₃ SiCH(C₃ H₇)N⁺[(C₄ H₈ O)₃ C₅ H₁₁ ](C₂ H₅)₂ Cl⁻

[C₁₀ H₂₁ (OC₂ H₄)₄ O]₃ SiCH(C₂ H₅)N⁺[(C₂ H₄ O)₆ COCH₃ ]₂ CH₃ Cl⁻

[H(OC₂ H₄)₁₆ O]₃ SiCH(C₈ H₁₇)P⁺(C₂ H₅)₂ C₆ H₄ C₄ H₉ Cl⁻

[CH₃ (OC₂ H₄)₁₆ O]₂ C₁₂ H₂₅ SiCH(CH₃)P⁺(C₃ H₆ COOH)₂ C₁₀ H₂₁ Cl⁻

[C₂ H₅ OC(OC₂ H₄)₅ O]₃ SiCH(CH₃)P⁺(C₂ H₄ OH) (CH₃)C₁₂ H₂₅ Cl⁻

[H(OC₂ H₄)₂ O]₃ SiCH(C₁₀ H₂₁)P⁺(O)⁻(CH₃)C₁₆ H₃₃

[h(oc₂ h₄)₂ o]₃ siCH(C₈ H₁₇)P⁺[(C₂ H₄ O)₆ H]₂ C₄ H₉ Br⁻

[CH₃ (OC₄ H₈)₂ O]₃ SiCH(CH₃)P⁺[(C₂ H₄ O)C₈ H₁₇ ](CH₃)₂ Cl⁻

[C₁₀ H₂₁ (OC₂ H₄)₂ O]₃ SiCH(C₆ H₁₃)S⁺(CH₃)C₁₀ H₂₁ Cl⁻

[H(OC₂ H₄)₁₄ O]₂ CH₃ SiCH(C₈ H₁₇)S⁺(C₂ H₄ COOH)C₁₈ H₃₇ Cl⁻

[H(OC₃ H₆)₄ O]₃ SiCH(C₁₄ H₂₉)S⁺(C₄ H₈ OH)C₆ H₅ Cl⁻

[CH₃ CO(OC₂ H₄)₃ O]₃ SiCH(C₂ H₅)S⁺(O)^(-C) ₁₈ H₃₇

[c₁₂ h₂₅ (oc₂ h₄)o]₃ siCH(C₃ H₇)S⁺[(C₃ H₆ O)H]C₆ H₁₃ Cl⁻

[H(OC₄ H₈)₄ O]₂ CH₃ SiCH(C₄ H₉)S⁺[C₂ H₄ O)₈ C₃ H₇ ]CH₃ Br⁻

[H(OC₂ H₆)₆ O](C₂ H₅ O)₂ SiCH(C₁₂ H₂₅)N⁺[(C₂ H₄ O)₁₀ H]₂ C₁₈ H₃₇ Br⁻

[C₁₄ H₂₉ (OC₂ H₄)₆ O](CH₃ O)₂ SiCH(CH₃)P⁺(C₃ H₆ COOH)₂ CH₃ Cl⁻

[H(OC₂ H₄)₁₀ O]₂ (C₃ H₇ O)SiCH(C₅ H₁₁)S⁺(CH₃)C₁₂ H₂₅ Cl⁻

When R₁ is

    (CH.sub.3).sub.3 Si

and a is 0, the compounds are prepared following the description givenfor the preparation of the above compounds with the exception that atris(trimethylsiloxy)silane is used as the starting reactant.Commercially available trihalosilanes and trimethylsilanes are used toproduce the starting reactant.

When a is 1 or 2, a corresponding organosilane compound where one or twoR₁ 's are alkyl is reacted with a trimethylchlorosilane at about 50° C.to 200° C. to produce the desired organosilane.

Illustrative compounds follow:

[(CH₃)₃ SiO]₃ SiCH(CH₃)N⁺(CH₃)₂ C₁₈ H₃₇ Cl⁻

[(CH₃)₃ SiO]₂ CH₃ SiCH(C₂ H₅)N⁺(C₂ H₄ OH)₂ C₆ H₄ CH₃ Cl⁻

[(CH₃)₃ SiO]₃ SiCH(C₄ H₉)N⁺(C₃ H₆ COOH) (C₄ H₉)₂ Cl⁻

[(CH₃)₃ SiO]₃ SiCH(C₂ H₅)N⁺(O)⁻(CH₃)C₁₀ H₂₁

[(ch₃)₃ siO]₃ SiCH(C₁₂ H₂₅)N⁺[(C₂ H₄ O)₁₀ H]₂ CH₃ Br⁻

[(CH₃)₃ SiO]₃ SiCH(C₃ H₇)N⁺[(C₄ H₈ O)₃ C₅ H₁₁ ](C₂ H₅)₂ C1⁻

[(ch₃)₃ siO]₃ SiCH(C₂ H₅)N⁺[(C₂ H₄ O)₆ COCH₃ ]₂ CH₃ Cl⁻

[(CH₃)₃ SiO]₃ SiCH(C₈ H₁₇)P⁺(C₂ H₅)₂ C₈ H₁₇ Cl⁻

[(CH₃)₃ SiO]₂ C₂ H₅ SiCH(CH₃)P⁺(C₃ H₆ COOH)₂ C₁₀ H₂₁ Cl⁻

[(CH₃)₃ SiO]₃ SiCH(CH₃)P⁺(C₂ H₄ OH) (CH₃)C₁₂ H₂₅ Cl⁻

[(CH₃)₃ SiO]₃ SiCH(C₁₀ H₂₁)P⁺(O)⁻(CH₃)C₈ H₁₇

[(ch₃)₃ siO]₃ SiCH(C₈ H₁₇)P⁺[(C₂ H₄ O)₆ H]₂ C₄ H₉ Br⁻

[(CH₃)₃ SiO]₃ SiCH(CH₃)P⁺[(C₂ H₄ O)C₈ H₁₇ ]₂ C₆ H₄ C₂ H₅ Cl⁻

[(CH₃)₃ SiO]₃ SiCH(C₆ H₁₃)S⁺(CH₃)C₁₆ H₃₃ Cl⁻

[(CH₃)₃ SiO]₂ SiCH(C₈ H₁₇)S⁺(C₂ H₄ COOH)C₆ H₅ Cl⁻

[(CH₃)₃ SiO]₃ SiCH(C₁₄ H₂₉)S⁺(C₄ H₈ OH)CH₃ Cl⁻

[(CH₃)₃ SiO]₃ SiCH(C₂ H₅)S⁺(O)^(-C) ₁₈ H₃₇

[(ch₃)₃ siO]₃ SiCH(C₃ H₇)S⁺[(C₃ H₆ O)H]C₁₂ H₂₅ Cl⁻

[(CH₃)₃ SiO]₂ C₁₈ H₃₇ SiCH(C₄ H₉)S⁺[(C₂ H₄ O)₈ C₃ H₇ ]CH₃ Br⁻

Siloxane oligomers of the organosilanes are formed from the monomers bythe controlled addition of from 1 to 100 equivalents of water,preferably in an inert solvent such as alcohol, tetrahydrofuran, etc. Asused herein, "oligomers" is used to mean a degree of polymerization offrom 2 to 100, preferably 2 to 20. A higher degree of polymerizationadversely affects the ability of the compound to bond itself to ametallic or vitreous surface as discussed below and is for this reasonavoided.

The above organosilanes are useful when used in a detergent compositionat a level of organosilane to water-soluble organic detergent of from2:1 to 1:10,000. When metallic or vitreous surfaces are washed or rinsedwith a detergent composition containing the above-describedorganosilane, a soil release benefit is imparted to the surface. It istheorized that the positively charged organosilane is attracted to thenegatively charged surface. The silicon atom in the organosilane canthen form a bond with the surface. The presence of the positive chargeon the organosilane is necessary to allow the bonding to take place froma dilute solution as is encountered in a detergent composition usagecontext and within a reasonable time period. The terminal alkyl groupsattached to the positively charged atom provides the soil releasebenefits. It is believed that the organosilane compound polymerizes onthe surface to form a thin coating of the polymer. The coating isresponsible for imparting the soil release benefits to the surface. Thatis, a hard surface having on it the polymeric coating will be soiled;however, the soil is not tenaciously bound to the surface by virtue ofthe coating and for this reason is easily washed away.

The following examples illustrate this invention.

EXAMPLE I

    (ch.sub.3 o).sub.3 siCH(CH.sub.3)N.sup.+(CH.sub.3).sub.3 Br.sup.-

One mole (163.5g.) of ethyl trichlorosilane is placed in a one literstirred Pyrex flask and irradiated with a 300 watt flood lamp. To thisis added slowly, a cold mixture of 1/4 mole of chlorine and 1/4 mole ofbromine so that a red-brown color is just maintained. When the additionis complete and the red color is gone, the residue is distilled out ofthe flask, yielding 1/2 mole of starting material, ethyltrichlorosilaneand about 1/2 mole of alphabromoethyltrichlorosilane.

One-half mole of the alpha-bromoethyltrichlorosilane (121.25g.) isplaced in a flask fitted with a stirrer, condensor, dropping funnel anda gas bubbler through which nitrogen is passed. 1.7 moles of absolutemethanol (54.4g) are added slowly such that the reaction temperaturedoes not rise above about 60° C.. When the methanol addition is completeand HCl evolution has ceased, the residue is distilled under reducedpressure to yield alpha-bromoethyltrimethoxysilane.

One quarter mole of the alpha-bromoethyltrimethoxysilane (57.3g) isplaced in an autoclave along with 17.7g of trimethylamine. The mixtureis heated to 80° C. for 6 hours under 200 p.s.i. nitrogen. The excesstrimethylamine is allowed to evaporate after the product has beenremoved from the autoclave, leaving the bromide salt ofalpha-trimethylammonioethyltrimethyoxysilane bromide.

Corresponding organosilanes where the nitrogen is phosphorus or sulfurare produced by substituting the trimethylamine with trimethylphosphineand dimethylsulfide, respectively.

EXAMPLE II

    [(ch.sub.3).sub.3 siO].sub.3 SiCH(CH.sub.3)N.sup.+(CH.sub.3).sub.3 Br.sup.-

The product of the above reaction, trimethylammonioethyltrimethoxysilanebromide, is heated to reflux with an excess of trimethylchlorosilaneuntil 3 equivalents of methylchloride is evolved. The resulting product,alpha-trimethylammonioethyl-tris-trimethylsiloxysilane bromide, isisolated by stripping out the residual volatile reactants.

EXAMPLE III

    (ch.sub.3 ch.sub.2 o).sub.3 siCH(C.sub.4 H.sub.9)N.sup.+(CH.sub.3).sub.2 CH.sub.2 C.sub.6 H.sub.5 Br.sup.-

In a manner like that used for the preparation ofalpha-bromoethyltriethoxysilane, alpha-bromoamyltriethoxysilane isprepared in two steps from amyltrichlorosilane (commercially available).One-quarter mole of alpha-bromoamyltriethoxysilane (78.5g) is refluxedfor 12 hours with 0.25 moles (33.75g) of benzyldimethylamine in 125 ml.of 2-butanone. The product,alpha-(benzyldimethylammonio)ethyltriethoxysilane bromide is isolated byremoving the solvent under vacuum.

EXAMPLE IV

    (ch.sub.3 och.sub.2 ch.sub.2 o).sub.3 siCH(CH.sub.3)N.sup.+(CH.sub.2 CH.sub.2 OCOCH.sub.3).sub.2 C.sub.12 H.sub.25 Br.sup.-

One-quarter mole of alpha-bromoethyltrichlorosilane is dissolved in 200ml. of dry hexane and sparged rapidly with nitrogen. 0.85 moles of thebeta-methoxyethanol is added slowly and the resulting mixture is stirreduntil the HCl evolution ceases. Distillation of the residue yieldsalpha-bromoethyltris(beta-methoxyethoxy)silane. This produce (0.2 moles)is heated with 0.2 moles of the diacetate ester of dodecyldiethanolamineat 135° C. for 16 hours to yield the desired quaternary ammonium salt.

What is claimed is:
 1. An organosilane having the formula ##STR15## orsiloxane oligomers thereof, wherein R₁ is an alkyl group containing 1 to4 carbon atoms,

    (CH.sub.3).sub.3 Si or Z(OC.sub.x H.sub.2x).sub.m

where x is 2 to 4, m is 1 to 20, Z is hydrogen, an alkyl groupcontaining 1 to 18 carbons or an acyl group containing 1 to 4 carbonatoms; a is 0 to 2; R₂ is an alkyl group containing 1 to 18 carbonatoms; R₃ is an alkyl group containing 1 to 18 carbon atoms; R₄ is analkyl, aryl or arylalkyl group containing 1 to 12 carbon atoms, acarboxy-substituted alkyl group containing 1 to 4 carbon atoms,

    (C.sub.x H.sub.2x O).sub.m Z

where x, m, and Z are as defined above, or oxygen provided only one R₄is oxygen and that when R₄ is oxygen, there is no X^(-;) R₅ is an alkyl,aryl or arylalkyl group containing 1 to 22 carbon atoms; X is halide;and Y is nitrogen, phosphorus or sulfur.
 2. The organosilane of claim 1wherein R₁ is an alkyl group.
 3. The organosilane of claim 1 wherein R₁is

    (CH.sub.3).sub.3 Si.


4. The organosilane of claim 1 wherein R₁ is

    Z(OC.sub.x H.sub.2x).sub.m.


5. The organosilane of claim 1 wherein a is 0 or
 1. 6. The organosilaneof claim 1 wherein the siloxane oligomer has a degree of polymerizationof from 2 to
 100. 7. The organosilane of claim 6 wherein the degree ofpolymerization is from 2 to
 20. 8. The organosilane of claim 1 whereinthe organosilane is a monomer.
 9. The organosilane of claim 1 wherein Xis chloride or bromide.
 10. The organosilane of claim 1 wherein R₃ ismethyl.
 11. The organosilane of claim 1 wherein R₄ is an alkyl groupcontaining 1 to 4 carbon atoms.
 12. The organosilane of claim 1 whereinR₅ contains 6 to 12 carbon atoms.
 13. The organosilane of claim 1 havingthe formula ##STR16## or siloxane oligomers thereof, wherein R₁ is analkyl group containing 1 to 4 carbon atoms, (CH₃)₃ Si or Z(OC.sub. xH_(2x))_(m) where x is 2 to 4, m is 1 to 20, Z is hydrogen, an alkylgroup containing 1 to 18 carbon atoms or an acyl group containing 1 to 4carbon atoms; a is 0 to 2; R₂ is an alkyl group containing 1 to 18carbon atoms; R₃ is an alkyl group containing 1 to 18 carbon atoms; R₄is an alkyl, aryl or arylalkyl group containing 1 to 12 carbon atoms, acarboxy-substituted alkyl group containing 1 to 4 carbon atoms,

    (C.sub.x H.sub.2x O).sub.m Z

wherein x, m and Z are as defined above, or oxygen provided only one R₄is oxygen and that when R₄ is oxygen, there is no X^(-;) R₅ is an alkyl,aryl, or arylalkyl group containing 1 to 22 carbon atoms; and X ishalide.